The instant invention relates to para-C.sub.5 alkyl-substituted ethoxycyclohexanes defined according to the structure: ##STR3## wherein R.sub.1, R.sub.2 and R.sub.3 represent the same or different methyl or hydrogen; and wherein R.sub.4 represents hydrogen, methyl or ethyl with the proviso that the sum of the carbon atoms in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is 2 and uses of same in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product.
Long-lasting, intense, substantive green, fresh cut grass-like, citrus, privet hedge (Ligustrum vulgare)-like, woody, floral, muguet, rose petal, balsamic and tomato leaf aromas with green, ozoney, woody, floral, muguet, rose, powdery, robusta coffee, dark cocoa, fruity, fatty-oily and tomato leaf topnotes and linden blossom, cucumber and melon-like undertones are highly desirable in several types of perfume compositions, perfumed articles and colognes (e.g., fruity and floral fragrances).
Perfume uses of ethoxycycloalkyl derivatives are well known in the literature. Thus, Arctander "Perfume and Flavor Chemicals (Aroma Chemicals)", Volume I, published in 1969 by the author at Monograph No. 713 discloses the compound having the structure: ##STR4## for use in perfumery. Arctander discloses that the compound having the structure: ##STR5## has a powerful, pungent-floral, deep-sweet, warm odor suggestive of ylang-ylang, pandanus and other exotic flowers. Arctander indicates that this compound is useful in perfume compositions of the heavy-floral type, in artificial ylang-ylang and in various types of soap perfumes and in general as a floralizer with considerable power. Arctander further states that the compound having the structure: ##STR6## has a "peculiar nut-like, or earthy undertone". Bielstein, Volume E II 6, 488, H6, System 530a, 522-523 (abstract of Le Brazidec, Bull. Soc. Chim. France[4], 31, 263) discloses that the compound having the structure: ##STR7## has an anisic aroma. The synthesis of this compound is disclosed by Le Brazidec and is further disclosed by Dutton, et al, Canadian Journal of Chemistry, 31 (1953), 1138, 1140. The structure: ##STR8## wherein R is methyl is shown by Bielstein, Volume E IV6 at page 3288 and is also disclosed at Chemical Abstracts, Volume 47, No. 2716h (abstract of J. Elisha Mitchell Sci. Soc., Volume 66, 171-4 (1950)). The compound having the structure: ##STR9## is also disclosed in Schoot, et al, U.S. Pat. No. 2,996,514.
The compounds having the structures: ##STR10## are indicated to be prepared by Chemical Abstracts, Volume 73, 1970, 66192c. The preparation of the compound having the structure: ##STR11## is also shown to be prepared by Bielstein, Volume E IV 6 at page 3280, Chemical Abstracts, 1961, 13386d (Zavgorodnii II) and Chemical Abstracts, Volume 49 (1955), No. 8848z (Zavgorodnii I).
Furthermore, the compound having the structure: ##STR12## is shown to be prepared by Zavgorodnii III at Chemical Abstracts, Volume 71 (1969), No. 3088m. the compound having the structure: ##STR13## is shown to be prepared using the compound having the structure: ##STR14## as a starting material according to the reaction: ##STR15## by Bielstein, E III 6, H6, 548. The compound having the structure: ##STR16## is shown to be prepared using as a starting material the compound having the structure: ##STR17## according to the reaction: ##STR18## by Bielstein, E IV 6, page 3378 and by Dutton, et al, Canadian Journal of Chemistry, 31 (1953), pages 1138, 1142.
The compound having the structure: ##STR19## is shown to be prepared by Bielstein, E III 6, H6, 505-6, System No. 530, abstract of Ipatieff, et al, Journal of American Soc., 60 (1938), 1161 and Bert, Bull. Soc. Chim., 37, 1252-70 (1925).
Copending Application for patent U.S. Ser. No. 08/428,420 filed on Apr. 25, 1995, Monteleone, et al describes 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes and mixtures thereof with bicyclopentadiene derivatives for use in perfumery and further discloses methods for preparing same. Said Application for patent U.S. Ser. No. 08/428,420 is a Divisional of Application for patent U.S. Ser. No. 08/299,966 filed on Sep. 2, 1994 now U.S. Pat. No. 5,462,923 having the same title. Both Ser. Nos. 08/299,966 and 08/428,420 disclose the compounds having the structures: ##STR20## for use in perfumery and further disclose that these compounds have "long-lasting, intense, substantive green, woody, privet hedge (Ligustrum vulgare)-like, floral, lilac, ozoney, fennel and anisic aromas with fruity, fresh green, ozoney, fresh air, "ocean breeze" and anisic topnotes".
Alkylcyclohexanols are known to be useful in the field of perfumery. Thus, "VERTENEX.RTM." is an article of commerce marketed by International Flavors & Fragrances Inc., said "VERTENEX.RTM." having the structure: ##STR21## Furthermore, "VERTENEX.RTM. HIGH CIS" is also an article of commerce marketed by International Flavors & Fragrances Inc., which has the structure: ##STR22## Furthermore, "ORIVONE", also an article of commerce marketed by International Flavors & Fragrances Inc., has the structure: ##STR23##
Para alkylcyclohexylalkyl ethers are known in the prior art. Thus, Eliel, et al, Chemical Abstracts, Volume 63, 1965, 3011g (abstract of J. Org. Chem. 30(3), pages 848-854) discloses the compound having the structure: ##STR24## Faillebin, Beilstein, Volume E II 6 at H7, No. 2, discloses the compound having the structure: ##STR25## (abstract of Faillebin, ANN. CHIM. 4, 156-82, 410-96 (1925)). Hiromu, et al, Chemical Abstracts, Volume 108, 1988 at monograph No. 108:62302g, discloses the compound having the structure: ##STR26## as being a component of an essential oil obtained from the root of Glycyrrhiza glabra (abstract of Nippon Nogei Kagaku Kashi 1987, 61(9), pages 1119-21 (Japan)). However, the aroma of this material is not disclosed nor is it indicated that the compound having the structure: ##STR27## contributes any aroma to the essential oil named.
Thus, nothing in the prior art discloses the unexpected, unobvious and advantageous organoleptic properties of the para-C.sub.5 alkyl-substituted ethoxycyclohexanes of our invention.